Ethanol → HCID 178474266, compound

HRID 493387

Reaction equation

HRID 493387 reaction equation
[O:1]([CH2:8][C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:27]=[CH:26][C:17]([O:18][C:19]3[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=3)=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CI.[CH2:37]([OH:39])[CH3:38]>>[O:1]([CH2:8][C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:27]=[CH:26][C:17]([O:18][C:19]3[CH:20]=[CH:21][C:22]([NH:23][C:37](=[O:39])[CH3:38])=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 8471TriethylamineHCID 178507748HCID 178507748, compound

Product 1

HCID 178474266HCID 178474266, compound

Procedure

4-{4-[2-(phenoxymethyl)-1H-imidazol-4-yl]phenoxy}aniline (600 mg, 0.00168 mol), (prepared according to a method analogous to that described in Example 28) is suspended in ethanol (30 ml) at 0° C. Triethylamine (0.235 ml, 0.00168 mol) and methyl iodide (0.136 ml, 0.0022 mol) are added. The mixture is stirred for 20 hours then evaporated to dryness. The residue obtained is adsorbed on silica then purified by chromatography on a Biotage-type silica column (eluent: ethyl acetate-heptane: 4-6 to 5-5). After washing with diethyl ether and isopentane, a beige-coloured powder is obtained.

Workup

  1. customthen evaporated to dryness
  2. customThe residue obtained
  3. customthen purified by chromatography on a Biotage-type silica column (eluent: ethyl acetate-heptane: 4-6 to 5-5)
  4. washAfter washing with diethyl ether and isopentane
  5. customa beige-coloured powder is obtained

Sources & evidence

ORD record
ord-b665d5e41fa942deb301be4134808e4c
Source dataset
uspto-grants-2009_05
Patent number
US07534805B2

Linked notes

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